# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 13:11:29 2020
#   Inital geometry file: a 151 line input string
#   Ligand name: [1-[2-(phenylsulfonylamino)ethyl]piperidin-4-yl]methyl 5-fluoranyl-2-methoxy-1~{H}-indole-3-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1[nH]c2ccc(F)cc2c1C(=O)OCC3CCN(CCN[S](=O)(=O)c4ccccc4)CC3
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 503  503  '[1-[2-(phenylsulfonylamino)ethyl]piperidin-4-yl]methyl 5-fluoranyl-2-methoxy-1~{H}-indole-3-carboxylate'  ligand  62  34  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_503
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 503  O4   O  OS    0  -0.655  -6.3177   2.2033  -2.0057
 503  S    S  S     0   1.374  -6.6287   1.8862  -0.6219
 503  O3   O  OS    0  -0.657  -7.5131   2.7501   0.1427
 503  C16  C  CR6   0  -0.197  -7.2783   0.2368  -0.5768
 503  C21  C  CR16  0  -0.232  -6.9720  -0.6470  -1.6039
 503  C20  C  CR16  0  -0.243  -7.4437  -1.9499  -1.5326
 503  C19  C  CR16  0  -0.236  -8.2118  -2.3558  -0.4498
 503  C18  C  CR16  0  -0.243  -8.5125  -1.4611   0.5699
 503  C17  C  CR16  0  -0.236  -8.0454  -0.1574   0.5130
 503  N2   N  NC1   0  -0.728  -5.2040   1.8569   0.1998
 503  C15  C  CH2   0  -0.297  -4.1359   0.9707  -0.2544
 503  C14  C  CH2   0  -0.274  -2.8300   1.4102   0.3968
 503  N1   N  NT    0  -0.424  -1.7353   0.5275   0.0510
 503  C13  C  CH2   0  -0.281  -0.4516   1.1969   0.1803
 503  C12  C  CH2   0  -0.428   0.6899   0.3072  -0.2846
 503  C22  C  CH2   0  -0.288  -1.7565  -0.6998   0.8304
 503  C23  C  CH2   0  -0.427  -0.6637  -1.6601   0.3899
 503  C11  C  CH1   0  -0.297   0.7120  -1.0071   0.4897
 503  C10  C  CH2   0  -0.141   1.7750  -1.9681  -0.0030
 503  O2   O  O2    0  -0.480   3.0539  -1.3665   0.2063
 503  C9   C  C     0   0.544   4.1383  -2.0322  -0.1942
 503  O1   O  O     0  -0.476   4.0815  -3.1155  -0.7383
 503  C8   C  CR5   0  -0.278   5.3505  -1.3051   0.1024
 503  C1   C  CR5   0   0.620   6.6308  -1.7571  -0.2074
 503  O    O  O2    0  -0.429   6.9311  -2.8885  -0.7999
 503  C    C  CH3   0  -0.463   8.3035  -3.2025  -1.0290
 503  C7   C  CR56  0   0.125   5.5253  -0.0280   0.7420
 503  C2   C  CR56  0   0.329   6.9101   0.2218   0.7793
 503  N    N  NR15  0  -0.767   7.5488  -0.8532   0.1926
 503  C6   C  CR16  0  -0.572   4.6609   0.9250   1.2871
 503  C5   C  CR6   0   0.550   5.2230   2.0612   1.8266
 503  F    F  F     0  -0.326   4.3994   2.9891   2.3541
 503  C4   C  CR16  0  -0.452   6.5903   2.3091   1.8600
 503  C3   C  CR16  0  -0.266   7.4574   1.3694   1.3258
 503  H1   H  HCR6  0   0.286  -6.3809  -0.3318  -2.4531
 503  H2   H  HCR6  0   0.274  -7.2126  -2.6463  -2.3272
 503  H3   H  HCR6  0   0.273  -8.5798  -3.3721  -0.4009
 503  H4   H  HCR6  0   0.274  -9.1148  -1.7765   1.4110
 503  H5   H  HCR6  0   0.285  -8.2853   0.5380   1.3061
 503  H6   H  HNC1  0   0.410  -5.3565   1.8263   1.2031
 503  H7   H  HCH2  0   0.243  -4.3636  -0.0746  -0.0236
 503  H8   H  HCH2  0   0.261  -4.0378   1.0584  -1.3357
 503  H9   H  HCH2  0   0.247  -2.5977   2.4158   0.0391
 503  H10  H  HCH2  0   0.205  -2.9646   1.4888   1.4891
 503  H12  H  HCH2  0   0.239  -0.4724   2.1064  -0.4246
 503  H13  H  HCH2  0   0.189  -0.2624   1.5119   1.2222
 503  H14  H  HCH2  0   0.218   0.5716   0.0976  -1.3534
 503  H15  H  HCH2  0   0.238   1.6279   0.8539  -0.1693
 503  H16  H  HCH2  0   0.192  -1.6379  -0.4847   1.9081
 503  H17  H  HCH2  0   0.239  -2.7258  -1.1881   0.7160
 503  H18  H  HCH2  0   0.237  -0.7085  -2.5562   1.0139
 503  H19  H  HCH2  0   0.221  -0.8527  -1.9748  -0.6417
 503  H20  H  HCH1  0   0.229   0.9039  -0.7883   1.5482
 503  H21  H  HCH2  0   0.236   1.7171  -2.9138   0.5437
 503  H22  H  HCH2  0   0.222   1.6275  -2.1831  -1.0660
 503  H23  H  HCH3  0   0.250   8.7734  -2.4739  -1.6921
 503  H24  H  HCH3  0   0.250   8.8589  -3.2659  -0.0916
 503  H25  H  HCH3  0   0.277   8.3134  -4.1752  -1.5104
 503  H26  H  HNR5  0   0.436   8.5487  -0.9331   0.0899
 503  H27  H  HCR6  0   0.266   3.5894   0.7896   1.2988
 503  H28  H  HCR6  0   0.276   6.9676   3.2232   2.2977
 503  H29  H  HCR6  0   0.278   8.5266   1.5347   1.3388

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 503  O3   S    double    1.454  0.020  1.454
 503  C21  C20  aromatic  1.388  0.020  1.388
 503  C21  C16  aromatic  1.389  0.020  1.389
 503  C20  C19  aromatic  1.388  0.020  1.388
 503  N2   S    single    1.645  0.020  1.645
 503  N2   C15  single    1.460  0.020  1.460
 503  S    C16  single    1.773  0.020  1.773
 503  S    O4   double    1.453  0.020  1.453
 503  C16  C17  aromatic  1.390  0.020  1.390
 503  C19  C18  aromatic  1.389  0.020  1.389
 503  C15  C14  single    1.524  0.020  1.524
 503  C17  C18  aromatic  1.386  0.020  1.386
 503  C14  N1   single    1.448  0.020  1.448
 503  C22  N1   single    1.454  0.020  1.454
 503  C22  C23  single    1.520  0.020  1.520
 503  N1   C13  single    1.453  0.020  1.453
 503  C13  C12  single    1.520  0.020  1.520
 503  C23  C11  single    1.526  0.020  1.526
 503  C11  C12  single    1.526  0.020  1.526
 503  C11  C10  single    1.515  0.020  1.515
 503  C10  O2   single    1.429  0.020  1.429
 503  O2   C9   single    1.334  0.020  1.334
 503  C9   O1   double    1.214  0.020  1.214
 503  C9   C8   single    1.444  0.020  1.444
 503  F    C5   single    1.348  0.020  1.348
 503  C6   C5   aromatic  1.378  0.020  1.378
 503  C6   C7   aromatic  1.397  0.020  1.397
 503  C5   C4   aromatic  1.390  0.020  1.390
 503  C8   C7   aromatic  1.439  0.020  1.439
 503  C8   C1   aromatic  1.393  0.020  1.393
 503  C7   C2   aromatic  1.408  0.020  1.408
 503  C4   C3   aromatic  1.386  0.020  1.386
 503  C1   O    single    1.312  0.020  1.312
 503  C1   N    aromatic  1.349  0.020  1.349
 503  C2   C3   aromatic  1.384  0.020  1.384
 503  C2   N    aromatic  1.381  0.020  1.381
 503  O    C    single    1.426  0.020  1.426
 503  C21  H1   single    0.930  0.020  1.080
 503  C20  H2   single    0.930  0.020  1.080
 503  C19  H3   single    0.930  0.020  1.080
 503  C18  H4   single    0.930  0.020  1.080
 503  C17  H5   single    0.930  0.020  1.080
 503  N2   H6   single    0.890  0.020  1.040
 503  C15  H7   single    0.970  0.020  1.090
 503  C15  H8   single    0.970  0.020  1.090
 503  C14  H9   single    0.970  0.020  1.090
 503  C14  H10  single    0.970  0.020  1.090
 503  C13  H12  single    0.970  0.020  1.090
 503  C13  H13  single    0.970  0.020  1.090
 503  C12  H14  single    0.970  0.020  1.090
 503  C12  H15  single    0.970  0.020  1.090
 503  C22  H16  single    0.970  0.020  1.090
 503  C22  H17  single    0.970  0.020  1.090
 503  C23  H18  single    0.970  0.020  1.090
 503  C23  H19  single    0.970  0.020  1.090
 503  C11  H20  single    0.970  0.020  1.090
 503  C10  H21  single    0.970  0.020  1.090
 503  C10  H22  single    0.970  0.020  1.090
 503  C    H23  single    0.970  0.020  1.090
 503  C    H24  single    0.970  0.020  1.090
 503  C    H25  single    0.970  0.020  1.090
 503  N    H26  single    0.860  0.020  1.020
 503  C6   H27  single    0.930  0.020  1.080
 503  C4   H28  single    0.930  0.020  1.080
 503  C3   H29  single    0.930  0.020  1.080

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 503  N2   S    C16  106.74  3.000
 503  C16  S    O3   108.46  3.000
 503  N2   S    O3   105.95  3.000
 503  C16  S    O4   107.79  3.000
 503  N2   S    O4   107.11  3.000
 503  O3   S    O4   120.09  3.000
 503  C17  C16  C21  121.40  3.000
 503  C17  C16  S    119.07  3.000
 503  C21  C16  S    119.49  3.000
 503  H1   C21  C20  119.98  3.000
 503  H1   C21  C16  121.04  3.000
 503  C20  C21  C16  118.98  3.000
 503  H2   C20  C19  120.20  3.000
 503  H2   C20  C21  119.62  3.000
 503  C19  C20  C21  120.18  3.000
 503  H3   C19  C18  119.87  3.000
 503  H3   C19  C20  119.87  3.000
 503  C18  C19  C20  120.26  3.000
 503  H4   C18  C17  119.60  3.000
 503  H4   C18  C19  120.23  3.000
 503  C17  C18  C19  120.17  3.000
 503  H5   C17  C18  119.99  3.000
 503  H5   C17  C16  121.00  3.000
 503  C18  C17  C16  119.01  3.000
 503  H6   N2   C15  113.51  3.000
 503  H6   N2   S    111.35  3.000
 503  C15  N2   S    119.27  3.000
 503  H8   C15  H7   107.76  3.000
 503  H8   C15  C14  108.89  3.000
 503  H7   C15  C14  111.32  3.000
 503  H8   C15  N2   109.02  3.000
 503  H7   C15  N2   111.21  3.000
 503  C14  C15  N2   108.59  3.000
 503  H10  C14  H9   106.53  3.000
 503  H10  C14  N1   111.84  3.000
 503  H9   C14  N1   108.79  3.000
 503  H10  C14  C15  109.82  3.000
 503  H9   C14  C15  107.92  3.000
 503  N1   C14  C15  111.72  3.000
 503  C22  N1   C13  110.73  3.000
 503  C13  N1   C14  111.45  3.000
 503  C22  N1   C14  112.05  3.000
 503  H13  C13  H12  106.75  3.000
 503  H13  C13  C12  109.07  3.000
 503  H12  C13  C12  109.41  3.000
 503  H13  C13  N1   111.49  3.000
 503  H12  C13  N1   108.50  3.000
 503  C12  C13  N1   111.50  3.000
 503  H15  C12  H14  106.96  3.000
 503  H15  C12  C11  111.43  3.000
 503  H14  C12  C11  109.38  3.000
 503  H15  C12  C13  108.65  3.000
 503  H14  C12  C13  109.22  3.000
 503  C11  C12  C13  111.10  3.000
 503  H17  C22  H16  106.54  3.000
 503  H17  C22  C23  109.00  3.000
 503  H16  C22  C23  109.17  3.000
 503  H17  C22  N1   109.54  3.000
 503  H16  C22  N1   110.90  3.000
 503  C23  C22  N1   111.56  3.000
 503  H19  C23  H18  107.17  3.000
 503  H19  C23  C11  109.88  3.000
 503  H18  C23  C11  110.51  3.000
 503  H19  C23  C22  109.30  3.000
 503  H18  C23  C22  108.85  3.000
 503  C11  C23  C22  111.03  3.000
 503  H20  C11  C10  108.50  3.000
 503  H20  C11  C23  107.81  3.000
 503  C10  C11  C23  109.87  3.000
 503  H20  C11  C12  108.67  3.000
 503  C10  C11  C12  113.05  3.000
 503  C23  C11  C12  108.81  3.000
 503  H22  C10  H21  107.97  3.000
 503  H22  C10  O2   110.22  3.000
 503  H21  C10  O2   109.77  3.000
 503  H22  C10  C11  110.23  3.000
 503  H21  C10  C11  110.40  3.000
 503  O2   C10  C11  108.26  3.000
 503  C9   O2   C10  118.26  3.000
 503  C8   C9   O1   125.50  3.000
 503  C8   C9   O2   111.67  3.000
 503  O1   C9   O2   122.82  3.000
 503  C7   C8   C1   105.98  3.000
 503  C1   C8   C9   124.23  3.000
 503  C7   C8   C9   129.79  3.000
 503  N    C1   O    123.78  3.000
 503  N    C1   C8   110.01  3.000
 503  O    C1   C8   126.21  3.000
 503  C    O    C1   118.86  3.000
 503  H25  C    H24  108.93  3.000
 503  H25  C    H23  108.96  3.000
 503  H24  C    H23  109.96  3.000
 503  H25  C    O    106.10  3.000
 503  H24  C    O    111.37  3.000
 503  H23  C    O    111.40  3.000
 503  C6   C7   C2   118.50  3.000
 503  C2   C7   C8   106.78  3.000
 503  C6   C7   C8   134.71  3.000
 503  C3   C2   N    129.07  3.000
 503  N    C2   C7   107.79  3.000
 503  C3   C2   C7   123.14  3.000
 503  H26  N    C2   124.30  3.000
 503  H26  N    C1   126.26  3.000
 503  C2   N    C1   109.44  3.000
 503  H27  C6   C5   120.26  3.000
 503  H27  C6   C7   122.17  3.000
 503  C5   C6   C7   117.57  3.000
 503  C4   C5   F    117.96  3.000
 503  C4   C5   C6   123.91  3.000
 503  F    C5   C6   118.13  3.000
 503  H28  C4   C3   120.72  3.000
 503  H28  C4   C5   120.24  3.000
 503  C3   C4   C5   119.03  3.000
 503  H29  C3   C4   120.67  3.000
 503  H29  C3   C2   121.48  3.000
 503  C4   C3   C2   117.85  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 503  CONST_01  C19  C20  C21  C16     0.00   0.0  0
 503  CONST_02  C19  C18  C17  C16     0.00   0.0  0
 503  CONST_03  C18  C19  C20  C21     0.00   0.0  0
 503  CONST_04  C18  C17  C16  C21     0.00   0.0  0
 503  CONST_05  C17  C16  C21  C20     0.00   0.0  0
 503  CONST_06  C17  C18  C19  C20     0.00   0.0  0
 503  CONST_07  C5   C6   C7   C8    180.00   0.0  0
 503  CONST_08  C3   C2   C7   C8    180.00   0.0  0
 503  CONST_09  N    C2   C7   C8      0.00   0.0  0
 503  CONST_10  C2   N    C1   C8      0.00   0.0  0
 503  CONST_11  C6   C7   C8   C1    180.00   0.0  0
 503  CONST_12  C2   C7   C8   C1      0.00   0.0  0
 503  CONST_13  C7   C2   N    C1      0.00   0.0  0
 503  CONST_14  C3   C2   N    C1    180.00   0.0  0
 503  CONST_15  C4   C5   C6   C7      0.00   0.0  0
 503  CONST_16  N    C1   C8   C7      0.00   0.0  0
 503  CONST_17  C4   C3   C2   C7      0.00   0.0  0
 503  CONST_18  C5   C6   C7   C2      0.00   0.0  0
 503  CONST_19  C5   C4   C3   C2      0.00   0.0  0
 503  CONST_20  C6   C7   C2   N     180.00   0.0  0
 503  CONST_21  C4   C3   C2   N     180.00   0.0  0
 503  CONST_22  C3   C4   C5   C6      0.00   0.0  0
 503  CONST_23  C3   C2   C7   C6      0.00   0.0  0
 503  CONST_24  C20  C21  C16  S     180.00   0.0  0
 503  CONST_25  C18  C17  C16  S     180.00   0.0  0
 503  CONST_26  C6   C7   C8   C9      0.00   0.0  0
 503  CONST_27  C2   C7   C8   C9    180.00   0.0  0
 503  CONST_28  N    C1   C8   C9    180.00   0.0  0
 503  CONST_29  C7   C8   C1   O     180.00   0.0  0
 503  CONST_30  C2   N    C1   O     180.00   0.0  0
 503  CONST_31  F    C5   C6   C7    180.00   0.0  0
 503  CONST_32  C3   C4   C5   F     180.00   0.0  0
 503  CONST_33  H2   C20  C21  C16   180.00   0.0  0
 503  CONST_34  H4   C18  C17  C16   180.00   0.0  0
 503  CONST_35  H3   C19  C20  C21   180.00   0.0  0
 503  CONST_36  H5   C17  C16  C21   180.00   0.0  0
 503  CONST_37  H1   C21  C20  C19   180.00   0.0  0
 503  CONST_38  H27  C6   C7   C8      0.00   0.0  0
 503  CONST_39  H26  N    C1   C8    180.00   0.0  0
 503  CONST_40  H29  C3   C2   C7    180.00   0.0  0
 503  CONST_41  H28  C4   C3   C2    180.00   0.0  0
 503  Var_01    C11  C23  C22  N1     57.13  30.0  1
 503  Var_02    C11  C12  C13  N1    -57.16  30.0  1
 503  Var_03    C23  C22  N1   C13   -58.98  30.0  1
 503  Var_04    C22  N1   C13  C12    58.95  30.0  1
 503  Var_05    C21  C16  S    O4     23.04  30.0  2
 503  Var_06    C7   C8   C9   O2      0.18  30.0  2
 503  Var_07    N    C1   O    C       0.69  30.0  2
 503  Var_08    C15  N2   S    C16    59.07  30.0  1
 503  Var_09    N1   C14  C15  N2    176.73  30.0  3
 503  Var_10    C8   C9   O2   C10  -179.19  30.0  3
 503  Var_11    H23  C    O    C1    -62.31  30.0  3
 503  Var_12    C14  C15  N2   S     163.95  30.0  3
 503  Var_13    H21  C10  O2   C9     61.26  30.0  1

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 503  chir_01  C11  C23  C12  C10  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 503  plan-1  S    0.020
 503  plan-1  C16  0.020
 503  plan-1  C21  0.020
 503  plan-1  C20  0.020
 503  plan-1  C19  0.020
 503  plan-1  C18  0.020
 503  plan-1  C17  0.020
 503  plan-1  H1   0.020
 503  plan-1  H2   0.020
 503  plan-1  H3   0.020
 503  plan-1  H4   0.020
 503  plan-1  H5   0.020
 503  plan-2  O2   0.020
 503  plan-2  C9   0.020
 503  plan-2  O1   0.020
 503  plan-2  C8   0.020
 503  plan-3  C9   0.020
 503  plan-3  C8   0.020
 503  plan-3  C1   0.020
 503  plan-3  O    0.020
 503  plan-3  C7   0.020
 503  plan-3  C2   0.020
 503  plan-3  N    0.020
 503  plan-3  C6   0.020
 503  plan-3  C5   0.020
 503  plan-3  F    0.020
 503  plan-3  C4   0.020
 503  plan-3  C3   0.020
 503  plan-3  H26  0.020
 503  plan-3  H27  0.020
 503  plan-3  H28  0.020
 503  plan-3  H29  0.020

